Recent advances in the rare-earth metal triflates-catalyzed organic reactions

ABSTRACT In the past three decades, rare-earth metal triflates including scandium triflate, yttrium triflate, and the lanthanide (La−Lu) triflate, were widely employed in the organic chemistry, such as cyclization, C-H bond functionalization and types of reactions. Recently, the approaches using rare-earth metal triflates as catalysts have been mainly focusing on (1) achieving the high regioselectivity and stereoselectivity with effective ligands and (2) further extending the reaction scope by cooperation with other transition metal catalysts. This review mainly focuses on recent advances in the rare-earth metal triflates-catalyzed organic reactions from 2017 to 2019. This review also emphasis on reaction transformations and related mechanisms to show the general readership about capabilities, challenges as well as potential applications.

[1]  Changwei Hu,et al.  Mechanism study on asymmetric Michael addition reaction between alkynone and α-angelica lactone catalyzed by chiral N, N'-dioxide-Sc(III) complex , 2020 .

[2]  K. Mori,et al.  Construction of seven- and eight-membered carbocycles by Lewis acid catalyzed C(sp3)-H bond functionalization. , 2019, Chemical communications.

[3]  Natsuki Ido,et al.  Highly Diastereoselective Synthesis of Medium-Sized Carbocycle-Fused Piperidines via Sequential Hydride Shift Triggered Double C(sp3)-H Bond Functionalization. , 2019, Organic letters.

[4]  S. Sieburth,et al.  Sequencing [4+1]-Cycloaddition and Aza-Michael Addition Reactions: A Diastereoselective Cascade for the Rapid Access of Pyrido[2',1':2,3]/Thiazolo[2',3':2,3]imidazo[1,5-a]quinolone Scaffolds as Potential Antibacterial and Anticancer Motifs. , 2019, The Journal of organic chemistry.

[5]  D. Werz,et al.  (4 + 3)-Cycloaddition of Donor-Acceptor Cyclopropanes with Thiochalcones: A Diastereoselective Access to Tetrahydrothiepines. , 2019, Organic letters.

[6]  C. Zheng,et al.  Enantioselective Synthesis of Arene cis-Dihydrodiols from 2-Pyrones. , 2019, Angewandte Chemie.

[7]  K. Laali,et al.  1-Aryltriazenes in the Suzuki, Heck, and Sonogashira Reactions in Imidazolium-ILs, with [BMIM(SO3H)][OTf] or Sc(OTf)3as Promoter, and Pd(OAc)2or NiCl2·glyme as Catalyst , 2019, European Journal of Organic Chemistry.

[8]  Pablo Domingo-Legarda,et al.  Visible light photocatalytic asymmetric synthesis of pyrrolo[1,2-a]indoles via intermolecular [3+2] cycloaddition. , 2019, Chemical communications.

[9]  K. I. Goldberg,et al.  Acid-Assisted Hydrogenation of CO2 to Methanol in a Homogeneous Catalytic Cascade System , 2019, ACS Catalysis.

[10]  Tong Zhang,et al.  Rare-Earth Y(OTf)3 Catalyzed Coupling Reaction of Ethers with Azaarenes. , 2019, Organic letters.

[11]  Xuyang Liu,et al.  Selective hydrodeoxygenation of biomass-derived furfural-acetone to prepare 1-octyl acetate , 2019, Green Chemistry.

[12]  S. Tu,et al.  Catalytic Three-Component Synthesis of Functionalized Naphtho[2,1-b]oxecines via a Double Bond Cleavage-Rearrangement Cascade. , 2019, Organic letters.

[13]  T. Cantat,et al.  Carbonylation of C-N Bonds in Tertiary Amines Catalyzed by Low Valent Iron Catalysts. , 2019, Angewandte Chemie.

[14]  V. Nesterov,et al.  Asymmetric Ring-Opening of Donor–Acceptor Cyclopropanes with Primary Arylamines Catalyzed by a Chiral Heterobimetallic Catalyst , 2019, ACS Catalysis.

[15]  A. Nishida,et al.  One-Pot Synthesis of Cycloocta[b ]indole Through Formal [5+3] Cycloaddition Using Donor-Acceptor Cyclopropanes , 2019, European Journal of Organic Chemistry.

[16]  Tong Zhang,et al.  Iodine‐Mediated Synthesis of Methylthio‐Substituted Catechols from Cyclohexanones , 2019, Advanced Synthesis & Catalysis.

[17]  B. Shen,et al.  Asymmetric Synthesis of α,β-Epoxy-γ-lactams through Tandem Darzens/Hemiaminalization Reaction. , 2019, Organic letters.

[18]  Shuai-Shuai Li,et al.  Cascade [1,5]-Hydride Transfer/Cyclization for Synthesis of [3,4]-Fused Oxindoles. , 2019, The Journal of organic chemistry.

[19]  C. Tung,et al.  Scandium-catalyzed electrophilic alkene difunctionalization: regioselective synthesis of thiosulfone derivatives , 2019, Organic Chemistry Frontiers.

[20]  Lili Lin,et al.  Chiral N , N ′‐Dioxide/Tm(OTf) 3 Complex‐Catalyzed Asymmetric Bisvinylogous Mannich Reaction of Silyl Ketene Acetal with Aldimines , 2019, Advanced Synthesis & Catalysis.

[21]  Hai‐Chao Xu,et al.  Continuous-Flow Electrosynthesis of Benzofused S-Heterocycles by Dehydrogenative C-S Cross-Coupling. , 2019, Angewandte Chemie.

[22]  S. Baskaran,et al.  A Domino Aza-Piancatelli Rearrangement/Intramolecular Diels-Alder Reaction: Stereoselective Synthesis of Octahydro-1 H-cyclopenta[ cd]isoindole. , 2019, Organic letters.

[23]  D. Werz,et al.  (3+3)-Annulation of Carbonyl Ylides with Donor-Acceptor Cyclopropanes: Synergistic Dirhodium(II) and Lewis Acid Catalysis. , 2019, Angewandte Chemie.

[24]  Xiaoming Feng,et al.  Asymmetric Synthesis of P-Stereogenic Compounds via Thulium(III)-Catalyzed Desymmetrization of Dialkynylphosphine Oxides , 2019, ACS Catalysis.

[25]  A. D. de Lera,et al.  A Computational Study of Model Parent Systems and Reported Aza-(Iso)Nazarov/Aza-(Iso)Piancatelli Electrocyclic Reactions , 2019, European Journal of Organic Chemistry.

[26]  Shanmugam Rajasekar,et al.  Cascade Rh(ii) and Yb(iii) catalyzed synthesis of substituted naphthofurans via transannulation of N-sulfonyl-1,2,3-triazoles with β-naphthols. , 2019, Chemical communications.

[27]  Haydar Kilic,et al.  The Reaction of Donor‐Acceptor Cyclopropanes with 4,7‐Dihydroindole: A New Protocol for the Synthesis of Divergent C2‐Alkylated Indoles , 2019, ChemistrySelect.

[28]  Lili Lin,et al.  Diversified Cycloisomerization/Diels-Alder Reactions of 1,6-Enynes through Bimetallic Relay Asymmetric Catalysis. , 2019, Angewandte Chemie.

[29]  Xiaohua Liu,et al.  Rh(I)/Sc(OTf)3-co-catalyzed Michael addition of ammonium ylide to (E)-1,4-enediones: synthesis of functionalized 1,4-diketones , 2019, Molecular Diversity.

[30]  Xiaoming Feng,et al.  Enantioselective Synthesis of 4-Hydroxy-dihydrocoumarins via Catalytic Ring Opening/Cycloaddition of Cyclobutenones. , 2019, Organic letters.

[31]  Yi Deng,et al.  Iridium-Catalyzed Enantioselective Allylation of Aryl Enamides and Enecarbamates. , 2019, Organic letters.

[32]  Z. Su,et al.  Bimetallic Catalytic Asymmetric Tandem Reaction of β-Alkynyl Ketones to Synthesize 6,6-Spiroketals. , 2019, Angewandte Chemie.

[33]  Z. Su,et al.  Bimetallic Catalytic Asymmetric Tandem Reaction of β-Alkynyl Ketones to Synthesize 6,6-Spiroketals. , 2019, Angewandte Chemie.

[34]  S. Tu,et al.  Synergistic silver/scandium catalytic spiroketalization of β-alkynyl ketones for the atom economical synthesis of skeletally diverse spirocyclic isochromenes , 2019, Organic Chemistry Frontiers.

[35]  K. Scheidt,et al.  Reductive annulations of arylidene malonates with unsaturated electrophiles using photoredox/Lewis acid cooperative catalysis , 2019, Chemical science.

[36]  Yudao Ma,et al.  Catalytic enantioselective oxidative coupling of saturated ethers with carboxylic acid derivatives , 2019, Nature Communications.

[37]  Limin Wang,et al.  Scandium(III) Trifluoromethanesulfonate Catalyzed Reactions of Donor-Acceptor Cyclopropanes with 1,1-Diarylethylenes , 2019, ChemistrySelect.

[38]  M. Xie,et al.  Thiourea participation in [3+2] cycloaddition with donor-acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes. , 2019, Chemical communications.

[39]  M. Xie,et al.  Highly Chemo- and Diastereoselective Dearomative [3 + 2] Cycloaddition Reactions of Benzazoles with Donor-Acceptor Oxiranes. , 2018, Organic letters.

[40]  Souvik Mandal,et al.  Lewis acid catalysis: regioselective hydroboration of alkynes and alkenes promoted by scandium triflate. , 2018, Chemical communications.

[41]  Jason M. Stevens,et al.  Direct Lewis Acid Catalyzed Conversion of Enantioenriched N-Acyloxazolidinones to Chiral Esters, Amides, and Acids. , 2018, The Journal of organic chemistry.

[42]  R. Batey,et al.  Lanthanide(III)-Catalyzed Synthesis of trans-Diaminocyclopentenones from Substituted Furfurals and Secondary Amines via a Domino Ring-Opening/4π-Electrocyclization Pathway. , 2018, Organic letters.

[43]  R. Balamurugan,et al.  Annulation of a Highly Functionalized Diazo Building Block with Indoles under Sc(OTf)3/Rh2(OAc)4 Multicatalysis through Michael Addition/Cyclization Sequence. , 2018, The Journal of organic chemistry.

[44]  Lili Lin,et al.  Asymmetric Synthesis of Tetrahydroindolizines by Bimetallic Relay Catalyzed Cycloaddition of Pyridinium Ylides. , 2018, Angewandte Chemie.

[45]  G. Evano,et al.  Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides. , 2018, Organic letters.

[46]  Ren‐Jie Song,et al.  [4 + 2] Annulation Cascades of 2-Bromo-1-arylpropan-1-ones with Terminal Alkynes Involving C-Br/C-H Functionalization. , 2018, Organic letters.

[47]  C. Afonso,et al.  Synthesis and Applications of Stenhouse Salts and Derivatives. , 2018, Chemistry.

[48]  M. Yamanaka,et al.  Construction of 1,3-Dithio-Substituted Tetralins by [1,5]-Alkylthio Group Transfer Mediated Skeletal Rearrangement. , 2018, Organic letters.

[49]  F. Manarin,et al.  Ytterbium (III) triflate/Sodium Dodecyl Sulfate: A Versatile Recyclable and Water‐Tolerant Catalyst for the Synthesis of Bis(indolyl)methanes (BIMs) , 2018, ChemistrySelect.

[50]  Qian Wu,et al.  Stereoselective Synthesis of Fully-Substituted Acrylonitriles via Formal Acylcyanation of Electron-Rich Alkynes. , 2018, Organic letters.

[51]  P. Yadav,et al.  Eosin Y–Yb(OTf)3 catalyzed visible light mediated electrocyclization/indole ring opening towards the synthesis of heterobiaryl-pyrazolo[3,4-b]pyridines , 2018 .

[52]  K. Mori,et al.  Highly Diastereoselective Synthesis of Tetralin-fused Spirooxindoles via Lewis Acid-catalyzed C(sp3)–H Bond Functionalization , 2018, Chemistry Letters.

[53]  Sivakumar Shanmugam,et al.  Er(OTf)3‐Catalyzed Multicomponent Synthesis of 3,4‐Dihydro‐2H‐pyran via Hetero‐Diels‐Alder Reaction under Ambient Temperature , 2018 .

[54]  A. Studer,et al.  Lewis Acid Catalyzed Stereoselective Dearomative Coupling of Indolylboron Ate Complexes with Donor-Acceptor Cyclopropanes and Alkyl Halides. , 2018, Angewandte Chemie.

[55]  Jiadong Hu,et al.  Highly Enantioselective Tandem Michael Addition of Tryptamine-Derived Oxindoles to Alkynones: Concise Synthesis of Strychnos Alkaloids. , 2018, Angewandte Chemie.

[56]  Huajian Xu,et al.  Selective Hydrogenolysis of Furfural Derivative 2-Methyltetrahydrofuran into Pentanediol Acetate and Pentanol Acetate over Pd/C and Sc(OTf)3 Cocatalytic System. , 2018, ChemSusChem.

[57]  M. Watkinson,et al.  Remarkable increase in the rate of the catalytic epoxidation of electron deficient styrenes through the addition of Sc(OTf)3 to the MnTMTACN catalyst. , 2018, Chemical communications.

[58]  F. Popowycz,et al.  The Piancatelli reaction and its variants: recent applications to high added-value chemicals and biomass valorization. , 2018, Organic & biomolecular chemistry.

[59]  Lili Lin,et al.  Diastereodivergent asymmetric Michael-alkylation reactions using chiral N,N′-dioxide/metal complexes† †Electronic supplementary information (ESI) available. CCDC 1411858, 1412691 and 1545249. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc02757e , 2017, Chemical science.

[60]  Lili Lin,et al.  Chiral N,N'-dioxide/Sc(OTf)3 complex-catalyzed asymmetric dearomatization of β-naphthols. , 2017, Chemical communications.

[61]  Lili Lin,et al.  Asymmetric Cycloaddition and Cyclization Reactions Catalyzed by Chiral N,N'-Dioxide-Metal Complexes. , 2017, Accounts of chemical research.

[62]  Guigen Li,et al.  Synergistic silver/scandium catalysis for divergent synthesis of skeletally diverse chromene derivatives. , 2017, Chemical communications.

[63]  Peng‐Fei Xu,et al.  Lewis acid catalyzed diastereoselective [3+4]-annulation of donor-acceptor cyclopropanes with anthranils: synthesis of tetrahydro-1-benzazepine derivatives. , 2017, Chemical communications.

[64]  Jieping Zhu,et al.  Fluorophores for Excited-State Intramolecular Proton Transfer by an Yttrium Triflate Catalyzed Reaction of Isocyanides with Thiocarboxylic Acids. , 2017, Angewandte Chemie.

[65]  Lili Lin,et al.  Highly Efficient Asymmetric Synthesis of Chiral γ-Alkenyl Butenolides Catalyzed by Chiral N,N′-Dioxide–Scandium(III) Complexes , 2017 .

[66]  S. Genovese,et al.  Ytterbium triflate promoted solvent-free synthesis of 2-amino-4H-pyranes , 2017 .

[67]  Lili Lin,et al.  Catalytic asymmetric Meerwein-Ponndorf-Verley reduction of glyoxylates induced by a chiral N,N'-dioxide/Y(OTf)3 complex. , 2017, Chemical communications.

[68]  Keshab Mondal,et al.  Lewis Acid Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes with γ-Hydroxyenones: Access to Highly Functionalized Tetrahydropyrans , 2017 .

[69]  D. Werz,et al.  A new golden age for donor-acceptor cyclopropanes. , 2014, Angewandte Chemie.

[70]  Stefan France,et al.  Intramolecular donor-acceptor cyclopropane ring-opening cyclizations. , 2014, Chemical Society reviews.

[71]  Ji-Chen Zhang,et al.  Highly Efficient Synthesis of Polysubstituted 1,2-Dihydroquinolines via Tandem Reaction of α-Ketoesters and Arylamines Catalyzed by Indium Triflate , 2011 .

[72]  Chao‐Jun Li,et al.  Sc(OTf)3-catalyzed direct alkylation of quinolines and pyridines with alkanes. , 2009, Organic letters.

[73]  F. Hampel,et al.  3,3'-Bis(trisarylsilyl)-substituted binaphtholate rare earth metal catalysts for asymmetric hydroamination. , 2006, Journal of the American Chemical Society.

[74]  Davidr . Evans,et al.  Enantioselective rare-earth catalyzed quinone Diels-Alder reactions. , 2003, Journal of the American Chemical Society.

[75]  M. Bradley,et al.  Mild and highly chemoselective oxidation of thioethers mediated by Sc(OTf)3. , 2003, Organic letters.

[76]  M. Sugiura,et al.  Rare-earth metal triflates in organic synthesis. , 2002, Chemical reviews.